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. Author manuscript; available in PMC: 2019 Mar 16.
Published in final edited form as: Org Lett. 2018 Mar 2;20(6):1604–1607. doi: 10.1021/acs.orglett.8b00344

Table 1.

Optimization of the Wacker Oxidationa

graphic file with name nihms971092u2.jpg
entry [Pd] AgX additive(s) yieldb (%)
1 Pd(PhCN)2Cl2 0
2 Pd(PhCN)2Cl2 AgOTf 33
3 Pd(PhCN)2Cl2 AgSbF6 39
4 Pd(PhCN)2Cl2 AgBF4 18
5 Pd(PhCN)2Cl2 AgNO3 40
6 Pd(PhCN)2Cl2 AgNO3 BQ 73
7c Pd(MeCN)4(BF4)2 BQ, KNO3 51
8 Pd(MeCN)4(BF4)2 BQ 59
9 Pd(MeCN)4(BF4)2 BQ, KNO3 71
10d Pd(PhCN)2Cl2 AgNO3 BQ 67
11e Pd(PhCN)2Cl2 AgNO3 BQ 80
a

Reaction conditions: substrate (60 μmol), naphthalene standard (12 μmol), [Pd] (6 μmol, 10 mol %), AgX (15 μmol, 25 mol %), benzoquinone (12 μmol, 20 mol %), Oxone (180 μmol, 3 equiv), water (50 μL), MeCN (400 μL), under air, room temperature.

b

Conversion and yield were determined by calibrated GC−FID analysis. Reactions were run in duplicate, and the average value is reported.

c

Reaction was conducted with 1.2 equiv of benzoquinone and no Oxone.

d

Reaction was run using double the volume of water (100 μL).

e

Oxone was added portionwise.